

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808022708/bt2751sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808022708/bt2751Isup2.hkl |
CCDC reference: 700583
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.007 Å
- R factor = 0.065
- wR factor = 0.155
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H2W2 .. H4O .. 2.08 Ang. PLAT731_ALERT_1_B Bond Calc 0.84(6), Rep 0.840(10) ...... 6.00 su-Ra O1 -H1O 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(6), Rep 0.838(10) ...... 6.00 su-Ra O3 -H3O 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(7), Rep 0.840(10) ...... 7.00 su-Ra O4 -H4O 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(5), Rep 0.841(10) ...... 5.00 su-Ra O5 -H5O 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(5), Rep 0.839(10) ...... 5.00 su-Ra O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(5), Rep 0.838(10) ...... 5.00 su-Ra O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(6), Rep 0.838(10) ...... 6.00 su-Ra O2W -H2W1 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.84(7), Rep 0.839(10) ...... 7.00 su-Ra O2W -H2W2 1.555 1.555 PLAT732_ALERT_1_B Angle Calc 109(8), Rep 109.5(18) ...... 4.44 su-Ra H2W1 -O2W -H2W2 1.555 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(6), Rep 0.840(10) ...... 6.00 su-Ra O1 -H1O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(6), Rep 0.840(10) ...... 6.00 su-Ra O3 -H3O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(7), Rep 0.840(10) ...... 7.00 su-Ra O4 -H4O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(5), Rep 0.840(10) ...... 5.00 su-Ra O5 -H5O 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(5), Rep 0.840(10) ...... 5.00 su-Ra O1W -H1# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(5), Rep 0.840(10) ...... 5.00 su-Ra O1W -H2# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(6), Rep 0.840(10) ...... 6.00 su-Ra O2W -H3# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(7), Rep 0.840(10) ...... 7.00 su-Ra O2W -H4# 1.555 1.555
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.31 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.58 Ang. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 4 PLAT732_ALERT_1_C Angle Calc 110(5), Rep 109.6(18) ...... 2.78 su-Ra H1W1 -O1W -H1W2 1.555 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.80(7), Rep 1.81(3) ...... 2.33 su-Ra H4O -O2W 1.555 3.577 PLAT736_ALERT_1_C H...A Calc 1.93(5), Rep 1.93(2) ...... 2.50 su-Ra H5O -O2 1.555 4.576 PLAT736_ALERT_1_C H...A Calc 1.98(5), Rep 1.98(2) ...... 2.50 su-Ra H1# -O2 1.555 4.586 PLAT736_ALERT_1_C H...A Calc 2.09(5), Rep 2.09(2) ...... 2.50 su-Ra H2# -O1 1.555 4.576 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 10 PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............ 5 Times
0 ALERT level A = In general: serious problem 18 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 23 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
3,4,5-Trihydroxybenzoylhydrazide (0.65 g, 3.5 mmol) and 5-bromo-2-hydroxybenzaldehyde (0.70 g, 3.5 mmol) were heated for 12 h in ethanol. The solvent was removed and the product recrystallized from ethanol.
Carbon and nitrogen-bound H-atoms were placed in calculated positions (C—H 0.95 Å; N–H 0.88 Å) and were included in the refinement in the riding model approximation, with Uiso(H) 1.2 Ueq(C). The hydroxy and water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 Å and H···H 1.37±0.01 Å.
The final difference Fourier map had a peak of 1.37eÅ-3 at 0.69Å from Br1 and a hole of -1.81eÅ-3 at 1.33Å from C2.
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
C14H11BrN2O5·2H2O | F(000) = 816 |
Mr = 403.19 | Dx = 1.779 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2758 reflections |
a = 30.8424 (8) Å | θ = 3.2–27.4° |
b = 3.7999 (1) Å | µ = 2.77 mm−1 |
c = 12.8484 (4) Å | T = 100 K |
β = 90.280 (2)° | Needle, colorless |
V = 1505.79 (7) Å3 | 0.30 × 0.03 × 0.03 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 3424 independent reflections |
Radiation source: fine-focus sealed tube | 2914 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −38→40 |
Tmin = 0.658, Tmax = 0.921 | k = −4→4 |
9964 measured reflections | l = −15→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0499P)2 + 10.2476P] where P = (Fo2 + 2Fc2)/3 |
3424 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 1.08 e Å−3 |
10 restraints | Δρmin = −1.82 e Å−3 |
C14H11BrN2O5·2H2O | V = 1505.79 (7) Å3 |
Mr = 403.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 30.8424 (8) Å | µ = 2.77 mm−1 |
b = 3.7999 (1) Å | T = 100 K |
c = 12.8484 (4) Å | 0.30 × 0.03 × 0.03 mm |
β = 90.280 (2)° |
Bruker SMART APEX diffractometer | 3424 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2914 reflections with I > 2σ(I) |
Tmin = 0.658, Tmax = 0.921 | Rint = 0.039 |
9964 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 10 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0499P)2 + 10.2476P] where P = (Fo2 + 2Fc2)/3 |
3424 reflections | Δρmax = 1.08 e Å−3 |
241 parameters | Δρmin = −1.82 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.467910 (16) | 0.31017 (16) | 0.89799 (4) | 0.01787 (17) | |
O1 | 0.32358 (12) | 0.6446 (12) | 0.5944 (3) | 0.0201 (9) | |
H1O | 0.3020 (15) | 0.745 (18) | 0.621 (5) | 0.030* | |
O2 | 0.20078 (11) | 0.9755 (11) | 0.6545 (3) | 0.0182 (8) | |
O3 | 0.05472 (13) | 1.3768 (13) | 0.7962 (4) | 0.0295 (11) | |
H3O | 0.0335 (16) | 1.36 (2) | 0.836 (5) | 0.044* | |
O4 | 0.05208 (14) | 1.1036 (15) | 0.9894 (4) | 0.0353 (12) | |
H4O | 0.048 (3) | 0.933 (15) | 1.030 (6) | 0.053* | |
O5 | 0.12324 (12) | 0.7692 (12) | 1.0737 (3) | 0.0182 (9) | |
H5O | 0.1471 (12) | 0.682 (18) | 1.092 (5) | 0.027* | |
O1W | 0.25912 (12) | 1.3152 (13) | 0.9988 (3) | 0.0209 (9) | |
H1W1 | 0.2444 (17) | 1.382 (18) | 1.050 (3) | 0.031* | |
H1W2 | 0.2806 (14) | 1.199 (17) | 1.020 (4) | 0.031* | |
O2W | −0.02887 (15) | 1.3435 (17) | 0.8657 (5) | 0.0506 (16) | |
H2W1 | −0.042 (3) | 1.30 (2) | 0.810 (4) | 0.076* | |
H2W2 | −0.038 (3) | 1.534 (14) | 0.890 (7) | 0.076* | |
N1 | 0.27850 (13) | 0.8683 (12) | 0.7531 (3) | 0.0139 (9) | |
N2 | 0.24174 (13) | 0.9859 (13) | 0.8027 (3) | 0.0138 (9) | |
H2N | 0.2431 | 1.0511 | 0.8684 | 0.017* | |
C1 | 0.35563 (16) | 0.5778 (15) | 0.6648 (4) | 0.0144 (10) | |
C2 | 0.39381 (16) | 0.4251 (16) | 0.6295 (4) | 0.0173 (11) | |
H2 | 0.3970 | 0.3730 | 0.5576 | 0.021* | |
C3 | 0.42746 (17) | 0.3479 (16) | 0.6985 (4) | 0.0193 (12) | |
H3 | 0.4535 | 0.2431 | 0.6743 | 0.023* | |
C4 | 0.42245 (16) | 0.4256 (16) | 0.8025 (4) | 0.0160 (11) | |
C5 | 0.38470 (16) | 0.5781 (15) | 0.8398 (4) | 0.0143 (10) | |
H5 | 0.3820 | 0.6294 | 0.9118 | 0.017* | |
C6 | 0.35065 (15) | 0.6562 (15) | 0.7712 (4) | 0.0126 (10) | |
C7 | 0.31105 (16) | 0.7988 (15) | 0.8138 (4) | 0.0130 (10) | |
H7 | 0.3089 | 0.8415 | 0.8865 | 0.016* | |
C8 | 0.20343 (16) | 1.0010 (13) | 0.7503 (4) | 0.0108 (10) | |
C9 | 0.16507 (16) | 1.0460 (15) | 0.8180 (4) | 0.0130 (10) | |
C10 | 0.12793 (16) | 1.2046 (16) | 0.7771 (4) | 0.0163 (11) | |
H10 | 0.1281 | 1.2984 | 0.7086 | 0.020* | |
C11 | 0.09101 (17) | 1.2242 (15) | 0.8368 (4) | 0.0176 (12) | |
C12 | 0.09010 (17) | 1.0775 (17) | 0.9364 (4) | 0.0204 (12) | |
C13 | 0.12713 (17) | 0.9146 (15) | 0.9777 (4) | 0.0152 (11) | |
C14 | 0.16479 (17) | 0.9040 (15) | 0.9188 (4) | 0.0149 (11) | |
H14 | 0.1903 | 0.8006 | 0.9468 | 0.018* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0094 (2) | 0.0195 (3) | 0.0247 (3) | −0.0001 (2) | −0.00302 (17) | −0.0020 (3) |
O1 | 0.0160 (18) | 0.032 (3) | 0.0125 (17) | 0.0031 (18) | −0.0028 (14) | −0.0016 (17) |
O2 | 0.0127 (17) | 0.027 (2) | 0.0148 (18) | −0.0039 (16) | −0.0015 (14) | 0.0021 (17) |
O3 | 0.0142 (19) | 0.041 (3) | 0.034 (2) | 0.0120 (19) | −0.0051 (17) | −0.005 (2) |
O4 | 0.016 (2) | 0.060 (4) | 0.030 (2) | 0.009 (2) | 0.0035 (18) | −0.013 (2) |
O5 | 0.0129 (17) | 0.031 (2) | 0.0110 (17) | −0.0007 (17) | 0.0027 (14) | −0.0045 (16) |
O1W | 0.0162 (18) | 0.035 (2) | 0.0113 (17) | 0.0027 (18) | 0.0015 (14) | −0.0044 (18) |
O2W | 0.016 (2) | 0.049 (4) | 0.087 (5) | 0.010 (2) | 0.010 (2) | 0.013 (3) |
N1 | 0.0107 (19) | 0.014 (3) | 0.017 (2) | −0.0016 (17) | 0.0010 (16) | −0.0008 (18) |
N2 | 0.0096 (19) | 0.019 (3) | 0.013 (2) | −0.0004 (18) | −0.0007 (15) | −0.0028 (18) |
C1 | 0.014 (2) | 0.016 (3) | 0.014 (2) | −0.002 (2) | −0.0013 (19) | −0.002 (2) |
C2 | 0.013 (2) | 0.025 (3) | 0.014 (2) | −0.001 (2) | 0.0024 (19) | 0.000 (2) |
C3 | 0.013 (2) | 0.020 (3) | 0.025 (3) | 0.001 (2) | 0.006 (2) | −0.003 (2) |
C4 | 0.012 (2) | 0.014 (3) | 0.021 (3) | −0.001 (2) | −0.003 (2) | 0.003 (2) |
C5 | 0.015 (2) | 0.013 (3) | 0.015 (2) | −0.001 (2) | 0.0005 (19) | −0.002 (2) |
C6 | 0.010 (2) | 0.015 (3) | 0.013 (2) | −0.003 (2) | 0.0008 (18) | 0.001 (2) |
C7 | 0.013 (2) | 0.015 (3) | 0.012 (2) | −0.006 (2) | 0.0022 (18) | −0.003 (2) |
C8 | 0.013 (2) | 0.004 (3) | 0.015 (2) | −0.0007 (18) | −0.0019 (18) | 0.0009 (19) |
C9 | 0.011 (2) | 0.013 (3) | 0.015 (2) | 0.000 (2) | −0.0027 (19) | −0.003 (2) |
C10 | 0.013 (2) | 0.016 (3) | 0.020 (3) | 0.001 (2) | −0.0034 (19) | 0.000 (2) |
C11 | 0.017 (2) | 0.013 (3) | 0.022 (3) | 0.008 (2) | −0.007 (2) | −0.007 (2) |
C12 | 0.012 (2) | 0.027 (3) | 0.022 (3) | 0.002 (2) | 0.001 (2) | −0.012 (2) |
C13 | 0.016 (2) | 0.017 (3) | 0.013 (2) | 0.001 (2) | 0.0025 (19) | −0.008 (2) |
C14 | 0.013 (2) | 0.016 (3) | 0.015 (2) | 0.001 (2) | −0.0022 (19) | −0.006 (2) |
Br1—C4 | 1.909 (5) | C1—C6 | 1.408 (7) |
O1—C1 | 1.361 (6) | C2—C3 | 1.393 (8) |
O1—H1O | 0.840 (10) | C2—H2 | 0.9500 |
O2—C8 | 1.236 (6) | C3—C4 | 1.378 (8) |
O3—C11 | 1.362 (6) | C3—H3 | 0.9500 |
O3—H3O | 0.838 (10) | C4—C5 | 1.388 (7) |
O4—C12 | 1.362 (7) | C5—C6 | 1.400 (7) |
O4—H4O | 0.840 (10) | C5—H5 | 0.9500 |
O5—C13 | 1.357 (7) | C6—C7 | 1.446 (7) |
O5—H5O | 0.841 (10) | C7—H7 | 0.9500 |
O1W—H1W1 | 0.839 (10) | C8—C9 | 1.482 (7) |
O1W—H1W2 | 0.838 (10) | C9—C10 | 1.395 (7) |
O2W—H2W1 | 0.838 (10) | C9—C14 | 1.403 (7) |
O2W—H2W2 | 0.839 (10) | C10—C11 | 1.378 (7) |
N1—C7 | 1.296 (7) | C10—H10 | 0.9500 |
N1—N2 | 1.378 (6) | C11—C12 | 1.396 (8) |
N2—C8 | 1.359 (6) | C12—C13 | 1.401 (8) |
N2—H2N | 0.8800 | C13—C14 | 1.390 (7) |
C1—C2 | 1.391 (7) | C14—H14 | 0.9500 |
C1—O1—H1O | 113 (5) | C5—C6—C7 | 118.3 (4) |
C11—O3—H3O | 111 (6) | C1—C6—C7 | 122.9 (5) |
C12—O4—H4O | 112 (6) | N1—C7—C6 | 120.1 (4) |
C13—O5—H5O | 110 (5) | N1—C7—H7 | 120.0 |
H1W1—O1W—H1W2 | 109.6 (18) | C6—C7—H7 | 120.0 |
H2W1—O2W—H2W2 | 109.5 (18) | O2—C8—N2 | 122.9 (4) |
C7—N1—N2 | 115.1 (4) | O2—C8—C9 | 123.0 (4) |
C8—N2—N1 | 120.0 (4) | N2—C8—C9 | 114.1 (4) |
C8—N2—H2N | 120.0 | C10—C9—C14 | 120.3 (5) |
N1—N2—H2N | 120.0 | C10—C9—C8 | 119.0 (5) |
O1—C1—C2 | 118.3 (5) | C14—C9—C8 | 120.4 (5) |
O1—C1—C6 | 121.6 (5) | C11—C10—C9 | 119.5 (5) |
C2—C1—C6 | 120.1 (5) | C11—C10—H10 | 120.2 |
C1—C2—C3 | 120.6 (5) | C9—C10—H10 | 120.2 |
C1—C2—H2 | 119.7 | O3—C11—C10 | 119.3 (5) |
C3—C2—H2 | 119.7 | O3—C11—C12 | 120.1 (5) |
C4—C3—C2 | 119.1 (5) | C10—C11—C12 | 120.6 (5) |
C4—C3—H3 | 120.5 | O4—C12—C11 | 116.7 (5) |
C2—C3—H3 | 120.5 | O4—C12—C13 | 123.0 (5) |
C3—C4—C5 | 121.5 (5) | C11—C12—C13 | 120.3 (5) |
C3—C4—Br1 | 119.2 (4) | O5—C13—C14 | 124.1 (5) |
C5—C4—Br1 | 119.3 (4) | O5—C13—C12 | 116.7 (5) |
C4—C5—C6 | 120.0 (5) | C14—C13—C12 | 119.2 (5) |
C4—C5—H5 | 120.0 | C13—C14—C9 | 120.0 (5) |
C6—C5—H5 | 120.0 | C13—C14—H14 | 120.0 |
C5—C6—C1 | 118.7 (5) | C9—C14—H14 | 120.0 |
C7—N1—N2—C8 | −167.2 (5) | N2—C8—C9—C10 | 154.0 (5) |
O1—C1—C2—C3 | −179.3 (5) | O2—C8—C9—C14 | 147.8 (5) |
C6—C1—C2—C3 | 0.1 (9) | N2—C8—C9—C14 | −31.4 (7) |
C1—C2—C3—C4 | −0.1 (9) | C14—C9—C10—C11 | 0.6 (9) |
C2—C3—C4—C5 | 0.1 (9) | C8—C9—C10—C11 | 175.2 (5) |
C2—C3—C4—Br1 | 178.5 (4) | C9—C10—C11—O3 | −179.5 (5) |
C3—C4—C5—C6 | 0.0 (9) | C9—C10—C11—C12 | −2.0 (9) |
Br1—C4—C5—C6 | −178.4 (4) | O3—C11—C12—O4 | −1.4 (8) |
C4—C5—C6—C1 | −0.1 (8) | C10—C11—C12—O4 | −178.9 (6) |
C4—C5—C6—C7 | 177.0 (5) | O3—C11—C12—C13 | 178.9 (5) |
O1—C1—C6—C5 | 179.4 (5) | C10—C11—C12—C13 | 1.4 (9) |
C2—C1—C6—C5 | 0.1 (8) | O4—C12—C13—O5 | 2.2 (9) |
O1—C1—C6—C7 | 2.5 (9) | C11—C12—C13—O5 | −178.1 (5) |
C2—C1—C6—C7 | −176.9 (5) | O4—C12—C13—C14 | −179.1 (6) |
N2—N1—C7—C6 | 176.8 (5) | C11—C12—C13—C14 | 0.6 (9) |
C5—C6—C7—N1 | −178.7 (5) | O5—C13—C14—C9 | 176.7 (5) |
C1—C6—C7—N1 | −1.8 (8) | C12—C13—C14—C9 | −1.9 (8) |
N1—N2—C8—O2 | −13.6 (8) | C10—C9—C14—C13 | 1.3 (8) |
N1—N2—C8—C9 | 165.7 (5) | C8—C9—C14—C13 | −173.2 (5) |
O2—C8—C9—C10 | −26.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.84 (1) | 1.91 (5) | 2.616 (6) | 141 (7) |
O3—H3o···O2w | 0.84 (1) | 1.96 (4) | 2.736 (6) | 153 (7) |
O4—H4o···O2wi | 0.84 (1) | 1.81 (3) | 2.623 (8) | 163 (9) |
O5—H5o···O2ii | 0.84 (1) | 1.93 (2) | 2.764 (5) | 171 (7) |
O1w—H1w1···O2iii | 0.84 (1) | 1.98 (2) | 2.812 (5) | 170 (6) |
O1w—H1w2···O1ii | 0.84 (1) | 2.09 (2) | 2.914 (6) | 167 (6) |
O2w—H2w1···O3iv | 0.84 (1) | 2.13 (5) | 2.845 (9) | 142 (8) |
O2w—H2w2···O4v | 0.84 (1) | 2.12 (4) | 2.900 (8) | 154 (8) |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+5/2, z+1/2; (iv) −x, y−1/2, −z+3/2; (v) −x, −y+3, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H11BrN2O5·2H2O |
Mr | 403.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 30.8424 (8), 3.7999 (1), 12.8484 (4) |
β (°) | 90.280 (2) |
V (Å3) | 1505.79 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.77 |
Crystal size (mm) | 0.30 × 0.03 × 0.03 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.658, 0.921 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9964, 3424, 2914 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.155, 1.22 |
No. of reflections | 3424 |
No. of parameters | 241 |
No. of restraints | 10 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0499P)2 + 10.2476P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.08, −1.82 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.84 (1) | 1.91 (5) | 2.616 (6) | 141 (7) |
O3—H3o···O2w | 0.84 (1) | 1.96 (4) | 2.736 (6) | 153 (7) |
O4—H4o···O2wi | 0.84 (1) | 1.81 (3) | 2.623 (8) | 163 (9) |
O5—H5o···O2ii | 0.84 (1) | 1.93 (2) | 2.764 (5) | 171 (7) |
O1w—H1w1···O2iii | 0.84 (1) | 1.98 (2) | 2.812 (5) | 170 (6) |
O1w—H1w2···O1ii | 0.84 (1) | 2.09 (2) | 2.914 (6) | 167 (6) |
O2w—H2w1···O3iv | 0.84 (1) | 2.13 (5) | 2.845 (9) | 142 (8) |
O2w—H2w2···O4v | 0.84 (1) | 2.12 (4) | 2.900 (8) | 154 (8) |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+5/2, z+1/2; (iv) −x, y−1/2, −z+3/2; (v) −x, −y+3, −z+2. |
This study extends the structural study on the Schiff base, 5-bromosalicylaldehyde benzoylhydrazone (Liu et al., 2006) as the title compound (Scheme I, Fig. 1) has several hydroxy groups on one of the aromatic rings. The compound crystallizes with two lattice water molecules. Hydrogen bonding interactions (Table 1) give rise to a layer motif.